1, 2-aliphatic-diamine thiosulphates and process of preparing them



UNITED STATES PATENT OFFICE 1,2-ALIPHATIC-DIAMINE THIOSULPHATES AND PROCESS OF PREPARING THEM Morris S. Kharasch, Chicago, 111., assignor toEli Lilly and Company, Indianapolis, Ind., a. corporation of Indiana No Drawing. Original application June 23, 1934,

Serial No. 732,088. Divided and this application April 22, 1936, Serial No. 75,751

6 Claims. (Cl. 260-127) It is the object of my invention to produce the nitrogen and for sulphur indicates that its forstable compounds 1,2-aliphatic-diamine thiomula is:

sulphates. (SiO|H)NHt-CH CHNH This present application is a division of my (2) 5 co-pending application Serial No. 732,088, filed 3 June 23, 1934 The 1,2-a11phatic-diamme sulphites which are The Lzmuphaficdiamine thiosulphates, to used for preparing the corresponding thiosulwhich this present application is directed, are also new w th me, but have been of special value in connection with the stabilizadescmbed m my co'pendmg applicatlon Serial tion of water solutions of water-soluble mer- 3 W 14, 1934- 10 curials, as set forth in said co-pending parent These ahphatlc'dlamine Sulphites may be P application; pared in various ways. Perhaps the most con- These 1,2-aliphatic-diamine thiosulphates may P K is causing the corresponding be prepared from the corresponding 1,2-aliphaticallpha'tlc'dlamm? to react with sulphur dioxide 15 iiiamine sulphites, as from 1,2-ethylenediamine or sulphutous acld; convemently by passing 15 sulphite or 1 2 1 i i sulpmte, by phur dioxide into either an absolute or aqueous additionally sulphurizing the sulphite' alcohol solution of the desired 1,2-aliphatic-di- This is conveniently done by heating the chosen amme F P as Lzflethylenediamine 3-1 Lg aliphatic diamme sulphite with sulphur, in pylenediamine) or into an acetone solution of boiling water, for one to two hours; then concenf e p the corresponding 20 trait-ling to a small volume (or to dryness) by aliphatic-diamine sulp te separates in solid form.

evaporation of the water (desirably under vacu- I claim as my invention! um); and then adding acetone, which precipi- A 1,2-aliphaticdiaminfiflfiosulphate.

tates the 1,2-aliphatic-diamine thiosulphate. 1,2-ethY1enediamine thiosulphate- This is collected on a filter, and may be crystallized -p py d a e t osulp ate. 25 from a small amount of water or alcohol-water The Process of Producing a -a I 'a iC-d mixture. 0n cooling it separates from that 501- ami th su p a which s sts n li th vent-mixture, in the form of beautiful white corresponding -di m e u ph te crystals. with sulphur in water.

1,2-ethylenediamine thiosulphate melts at 218 T e Process of producing 1,2-ethY d 30 0., with decomposition. An analysis of it for amin thi su1p t ,w =h s stsi b ilin 1,2- nitrogen and for sulphur indicates that its formula ethylenediamine sulphite With Sulphur in W t is: 6. The process of producing 1,2-propylene-diamine thiosulphate, which consists in boiling 1,2- (1) (S2O3H) NH3 CH2 CHZ NH2 propylenediamine sulphite with sulphur in water. 5

1,2-propylenediamine thiosulphate melts at 186 0., with decomposition. An analysis of it for MORRIS S. KHARASCI-I. 

